Tailwinds - Upscale Oceanfront! Stunning Views!

Photo gallery for Tailwinds - Upscale Oceanfront! Stunning Views!

A covered outdoor seating area with wicker furniture and a view of a lake.
A dining area with a round table and four chairs, large windows with a view of the sea, and a wooden floor.
A large, two-story house with a porch and a well-maintained lawn.
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.
A kitchen with a double sink, two windows, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Discover nearby landmarks
    Close to Linekin Bay

Popular amenities

  • Balcony
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine

Explore the area

View in a map
Boothbay, ME
  • Place, Linekin Bay
    ‪2 min walk‬
  • Place, Boothbay Harbor Marina
    ‪9 min drive‬
  • Place, Coastal Maine Botanical Gardens
    ‪12 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪33 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Mudroom

1 Single Bed

Queen 3

1 Queen Bed

Twin

2 Single Beds

Waterfront Queen 1

1 Queen Bed

Waterfront Queen 2

1 Queen Bed

5 bathrooms

Downstairs Bathroom

Toilet · Shower only

Queen 1 en-suite

Toilet · Shower only

Queen 2 en-suite

Toilet · Shower only

Queen 3 en-suite

Toilet · Shower only

Upstairs Hallway Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

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About the area

East Boothbay

Located in East Boothbay, this holiday home is on the waterfront. Ovens Mouth Preserve and Linekin Bay reflect the area's natural beauty and area attractions include Coastal Maine Botanical Gardens and Opera House at Boothbay Harbor. Maine State Aquarium and Boothbay Railway Village are also worth visiting. Discover the area's water adventures with kayaking and snorkelling nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
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Map
Boothbay, ME

What's nearby

  • Linekin Bay - 2 min walk - 0.2 km
  • Opera House at Boothbay Harbor - 9 min drive - 8.3 km
  • Boothbay Harbor Marina - 9 min drive - 8.7 km
  • Coastal Maine Botanical Gardens - 12 min drive - 12.2 km
  • Bowdoin College - 51 min drive - 66.3 km

Getting around

  • Wiscasset, ME (ISS) - 32 min drive

Restaurants

  • ‪Circle K - ‬7 min drive
  • ‪South Bristol Fisherman's Coop - ‬62 min drive
  • ‪Boothbay Lobster Wharf - ‬9 min drive
  • ‪Tugboat Inn - ‬9 min drive
  • ‪Robinson's Wharf - ‬12 min drive

Frequently asked questions

Is Tailwinds - Upscale Oceanfront! Stunning Views! pet-friendly?

No, only service animals are welcome at the property.

How much is parking at Tailwinds - Upscale Oceanfront! Stunning Views!?

On-site parking is available at the property.

What time is check-in at Tailwinds - Upscale Oceanfront! Stunning Views!?

Check-in begins at 4:00 PM.

What time is check-out at Tailwinds - Upscale Oceanfront! Stunning Views!?

Checkout is at 10:00 AM.

Where is Tailwinds - Upscale Oceanfront! Stunning Views! located?

Situated on the waterfront, this holiday home is steps from Linekin Bay and 2.4 mi (3.8 km) from Grimes Cove Beach. Carousel Music Theater and Boothbay Region Land Trust are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very clean. It was spacious and comfortable. The kitchen was well organized and supplied with plenty of amenities.
Stayed 14 nights in Aug 2026
From a partner site

10/10 Excellent

Beautiful Maine Setting

The house was spotless, well equipped, attractively and comfortably furnished. The extensive decking was generously furnished and a delight to sit peacefully and watch the boats in the bay at any time of day. We enjoyed learning about the remarkable history of the property and we were fascinated by the old pictures displayed. Our host, Pam, was completely responsive to any of our questions and check-in and check-out was easy. Thank you for sharing this lovely home.
From a partner site

10/10 Excellent

Tailwinds Home

Pam and her team are professional and accessible! Beautiful 19th century home in East Boothbay! The 4 bedrooms, plus a single bed tucked into a downstairs nook was so accommodating for a large family. 5 full bathrooms, one being on first floor, a real luxury! Wrap around porch overlooking a huge yard and Linekin Bay is delightful.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends reunion

We had a fabulous time during our recent visit to Boothbay Harbor, our stay at Tailwinds was wonderful. The home is beautiful, well appointed, clean and comfortable with a stunning view of the inlet. East Boothbay is just a short drive to Boothbay Harbor, the location worked very well for us. We loved hanging out on the back decks and enjoying the peaceful view. Our group of 4, we are long-time friends, enjoyed the 4 bedrooms with our own bathroom to use during our stay, we all found the beds to be very comfortable. While we didn't need to contact Pam during our stay, she had provided clear instructions on how to contact her. We all agreed that we would definitely consider staying here again next year.
Stayed 3 nights in Jun 2025
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